Encounters of me coming out sexually wise, later in life, installment 1

These are going to be a unique set of stories that I wanted to do in order to sort of memorialize and give a diary of a guy, me, who officially tried to come out ‘later’ in life sexually wise, it never actually ever came to happen ‘earlier’ for various reasons that I may or may not share. I have always pretty much lived my life as a gay man, albeit without any sex or any sexual encounter, etc, with another guy. I’m a bit older than the normal guy who had no issues in seeking sex, taking risks of rejection, fumbling along and doing it right or wrong I have never shyed away from being gay, having gay friends, going to gay films, a few clubs and bars throughout my life. I just never allowed myself relationships in any way, not even hook ups. It was always my secret, nobody I knew ever knew, but then again I never had a huge posse of friends, and have moved cities from time to time always hoping I would do something to get my life in gear.I realize the stories I am going to tell will not sit well with some of you. I know most of you are out and proud and have had healthy gay relationships. You’ve taken the good with the bad. I am fully aware that I have issues and have had issues and could definitely benefitted from therapy of sorts. Ya think?. It is like the 40 year old virgin, although I wont say my age or location. It just never happened and that is all that is before me and what I have to deal with. Time just goes by and there you are.

Feel free to comment on whatever you’d like. You don’t know me and what I’ve gone through nor will ever know me. But I felt a need to write this out on my odd journey to figure things out. There may be some who may relate in a way, or some who will not. Honestly, I wish I had gone to a gay bar, found some guy and went back to his place, and had full one on one sex, but I pretty much lacked that courage to do that. For years, If I guy ever showed interest in me, I’d do something to ruin that. I guess I played games and after years of doing that, it just became somewhat normal and what I was used to doing. Yes, therapy would have been good. I grew up in a dysfunctional family, and overweight much of my life, slimmed down at 18, gained a lot in my late 20s and am slimming down again. Maybe these encounters will help me to do that. It simply just got to the point in my life where I was at Point A and needed to get to Point G and had to start somewhere. The time had long past where I felt I was going to meet someone magically and have that beautiful first time sex . If didn’t do something and soon, well, it would just get harder and harder, and for me, it was like this layer of glass always was between me and that part of my life and I just never knew how to break past it.

The first encounter. Early Dec 2011.

One evening, I was walking back from downtown through an area known for bars and a few clubs. I just felt something was in the air and expected something to happen. Anything. As I turned one corner, this cute mixed race guy on a bike riding up the sidewalk caught my eye, and I smiled. I don’t usually do that, but then he said “hey, where you heading” and I knew at that moment something was going to be different. I turned around and said “just heading home” as I lived a few blocks away. He said “do you want some company?” and I said “well, I don’t know. I gotta get up early”. It was only 8:30 pm ha ha, but he stood there talking, sitting on his bike and was saying things like “I really need some company” and ‘youre good looking”. He must have been 20 or 21 years old. Cute, short dark hair and tight body. Wasn’t disheveled or poor looking at all. A little rough around the edges. I could tell he must have spent some time on the streets or living with family and had to get out of the house for the most part. It was funny, at one point he asked if I liked to party and started to unbutton his jeans (oh my) but then pulled out this small metal pipe. Uh oh I thought, I m sure that pipe was something I didn’t want to be associated with. Then he started to hustle me and asking “you know for $40 we could go to this arcade around the corner and get a room. I know the owner who’ll rent a small room out”. He was persistent as I was hesitant and to him, half way there. I told him I didn’t feel comfortable with that but I have never been against the thought of paying someone for sex. I knew it was an eventual option and I ve often thought it to be akin to therapy in a sense. If you have to do it who’s to criticize. If it helps you get from A to Z, then you gotta do what you gotta do.Well next, I figured I had nothing to lose and looking back, temporarily lost all good sense and said to him” how bout we go down a few blocks into that alley and I ll give you $20 to make out with me”. As desperate as that may sound, I was. Here was something looking at me and I had this courage to break through this glass wall as crazy as this all sounds (and admittredly dangerous as well). We proceeded south a few blocks to the alley, he on his bike riding circles around me, me on foot wondering what I had gotten myself into. We got into the alley and sat down behind this green plastic dumpster. Im being honest in saying the alley and the area was exceptionally clean. No trash, no rodents, very very clean. I call it an alley, but it was simply an area between two buildings one half block from an Irish bar. We sat down next to each other on this raised area and he lifted up his shirt to reveal a beautiful brown body and two nice dark nipples. Washboard abs too. I used my thumb and forefinger to touch his nipples, rolling them in my fingers and gently sqeueezing. I reached my head over and gently kissed his nipples and had my hand on his tight belly, sort of stroking his abs. Abs and nipples. What a great combo. It felt really good and I was amazed how hard and soft at the same time everything felt. I could have used a loss of a few pounds myself and was not in that tight of a body image .Anyway, I positioned my head closer to his and tried to go in for a kiss, but he turned his head away. I had already given him $10 of the promised $20 so I wasn’t sure what was up. Yes, I realized all along this guy was a hustler of sorts, maybe not a prostitute, but just a guy who was street savvy and knew what a hungry guy like me was after. He told me if we went back to that arcade we could do a whole lot more. I declined again and said here is the other $10.00. He took it lol and still would not kiss. He started to get up and said he didn’t feel comfortable in this alley. In retrospect, I don’t blame him and realized if the cops had driven down there to randomly check and discovered us, and he with his pipe in this pants, uh oh, that would not have been a good situation. It didn’t dawn on me until we got up to walk away that it could have turned out differently. And not in a good way. I also did not know this guy. He could have had a knife, a friend nearby, he could have robbed me. I am much taller than him, but still. So we got up and started to walk out of the alley and he asked again if I wanted to go to that arcade and so more, but I really did not want to be caught with 1. He and his pipe in a room like that. 2. In an arcade that I knew nothing about. It’s a gaming place, very sparsely used, but I guess the owner has a few rooms that he lets use. I assume for hookers I don’t know. Lol. That was new to me. I am no prude and have seen and been aware of many things in my life. I gave him my number and said to call me and I could gift him with a little help if he wanted to try again at my place. Again, I realize not the best idea and yes, a form of prostitution. I’ve never had an issue with anybody paying someone for sex or for someone taking money for it, but I was never comfortable with the drug aspect. He said smoking it makes him hard and cum better. I had read too, that guys who smoke that stuff have a cum smell that tastes nas

(this got cut off from the above post). smoke that stuff have a cum smell that tastes nasty so it wasn’t something I was anxious to try, ha ha.

So we parted way, he again driving circles around me as I walked. I got a little attached for a few moments and wished he was coming back to my place, but I knew that wasn’t the best idea. I went home, he went his way and I thought, my god, I touched a guy and played with his body. After all this time. The next day, I got a few phone calls from a number I didn’t know, and assume it may have been him, but I never answered and never ran into him again.

Next: Chapter two: Navy Hottie Chris

Installment 2: Navy Hottie Chris: December 2011

After that last encounter, I knew I had to get my ass in gear and do ‘something’ to maybe get out of my comfort zone. Make changes, get out there more, maybe join some dating sites. I knew potential encounters had always been around me, for years, it’s just I never reacted on them or ignored them or the guy.

I looked around at some dating sites, and joined POF and OK Cupid and put a profile in. I was really just testing the waters with these and sites like Scruff, Grindr and Manhunt would eventually come later, but for now I was comfortable putting my photo up and seeing what happened. Now I would NEVER contact a guy on my own lol (the story of my life) and would get some hits, a few guys would contact me but it never went anywhere.

One day I received a contact from a guy on the site who said “hey, just wanted to let you know OKC put both of us as a match, but I am straight”. I wrote him back and said something to the effect of “oh wow, that IS strange”. Funny because I looked at his profile and our match was 0% so I wasn’t sure what he was talking about. He was cute too. About 27, really nice body and looked like a young Mario Lopez to be honest. He had about 3 pix on his profile and one was shirtless with some very nice nipples and a built chest. Wow I was thinking. But this was not going anywhere I said. He was in the Navy and dated lots of girls he said. So basically I put him aside in my mind after that last contact. He wrote again a few days later and asked some random question that I don’t remember, but we got to chatting and I was very bold and wanted to know info on what he did with girls and if girls like to play with guys nipples or do they rim or other things like that. He was very receptive too and asked a few questions of me. Obviously I am no expert, but damn if I had not watched enough porn or read enough porn in my life to have a good idea of what went on. He was into our discussion and would make comments like “I hear gay guys have lot s of women friends”. And “maybe you can go with me to a club one day” because I told him I had gone to a few clubs with friends who were girls and they hit on guys and I did the same thing. Lying out of my teeth actually loll. But I said I’d go if “you come to one of mine one day “ . For a few weeks it went banter like that until one day he wrote and said “You know, I have to admit something to you. I’ve always been curious about…” and immediately when I read that a gulp went down my throat. OMG what was he going to say?? I read on and it was what I expected. “… I’ve always been curious about what it would be like with a guy and was wondering if you’d be willing to help me get my feet wet in this”. ME? I thought, but not without saying to myself “OMG ME???? HE’s so f’ing hot and young. Why the hell me???” For some reason, I thought he was coming out to me so the nurturing part of me was like “Hey you need to talk? Wanna get it out and we can get a drink and you can talk”, but he was like ‘oh no, I’m fine. “ “Just want to know if we can get together and ‘chill’ as he put it and “see what happens”. GULP again I was so nervous about that. Here I was the one with no experience and he was asking me to get his feet wet in a gay encounter. Ha ha, . But I said Yes. Of course we can get together.

This was by now around New Years 2011 and I remember him contacting me, (by now he had my text number) and asking if we could ‘chill’ tonight. My place was a mess and I was not ready to receive anybody and I knew in saying “not tonight” I would risk losing the opportunity. And yes, this was New Years Eve, but I said it was not a great night and he said he’d contact me tomorrow. Immediately I went into cleaning my place, then I went to the sex shoppe in town and bought some lube and flavored lube for god knows what. I literally had no idea what he wanted and what was going to happen. I know he said it would be nothing too ‘heavy’ so I didn’t think anal would come into play, but I had no idea what to expect. I even briefly thought for a bit that it was a scam and he’d have another navy guy waiting and they’d come up and bash me or rob me or something. My mind went all over the place.

But the next day, I waited and heard nothing. Then around 4 pm I texted him and said “hey what’s up” and he said he was at the lake and would be heading home in a bit and would text me. But later when he got home he asked how was the parking in my area and then said he’d call me later. I heard nothing and thought I had lost my chance. The next day he texted and apologized and said we’d ‘chill’ another time. I was kind of disappointed however and cursed myself for not letting him come that first night.

Another missed opp later and then finally I guess about a week and a half later he finally contacted me again while I was at work , I think it was a Monday, and asked if I was busy that night and wanted to know if I was ‘down’ to hang out. I was not so ‘up’ on his lingo and tried to be cool. I was yes, and said he’d shower, eat and be over in about an hour and a half. GULP again, it was going to happen. I don’t know what, but something was going to happen with this hottie Navy guy. Anyway, he arrived on time or so and he came up to my place. He was wearing a hoodie, jeans, flip flops and a t shirt underneath. He came up and went to my bedroom and sat on one side of my bed while I sat on the other. We both kind of looked at each other form opposite sides of the bed, it was kind of funny to be honest. We started talking and me saying things like Have you ever done anything with a guy and him saying “no” but he was always curious . I could tell , even though he seemed very open, that some of his views were formed by being in the navy and probably by his buddies and what he may have heard about being gay or something. But he asked questions like “have I ever heard of guys who purposely infect other guys with HIV” and that he hear d that things can slip inn thru the urethra of th e penis and he was concerned about that. Sort of a bit paranoid I surmised,, but not overly so. I had no idea what to expect . He was straight and I had not spent a lot of time in my life talking to straight guys about sex and especially military guys. So anyway, he says we should get started and he comes over to my side and lies down and takes off his shirt. His shoes were off already. Without saying, I knew anything over the neck was out of bounds, ie. No kissing. I have to say here that a lof of our previous conversations was about body worship, nipple play, ass etc, So I begin to kiss his body all over, his underarm pits (luckily no deodorant on him), his nipples, kissing them, licking them and sucking them, biting them gently and I ‘d use my hadn to all over his tight belly . I got down to where his jeans buttoned and felt along that area, the tight area of his groin and slipped my fingers down and noticed he had shaven down there. I did’t really think this was a straight guys thing to do and I asked him about it and he said “he likes to keep things neat down there and that that he worked out a lot and it just felt better or something like that. I ws kind of hopig for a full bush of hair down there, but then he said “oh w